3,5-Dinitro-L-tyrosine is a naturally occurring, proteinogenic amino acid derivative in the tyrosine family, featuring a phenolic side chain bearing two nitro substituents at the 3- and 5-positions. The molecule contains an α-amino group and a carboxyl group on the amino acid backbone, with the side chain retaining a phenolic functionality while the nitro groups introduce strong electron-withdrawing character and alter aromatic reactivity; the name specifies the L stereochemical configuration. In research and synthetic workflows, this dinitro-substituted tyrosine analogue is used as a substrate or building block for peptide and conjugate preparation, where the activated aromatic ring and altered physicochemical properties support labeling, structure-activity studies, and chemical biology investigations involving tyrosine-derived motifs.
CAT No: CP18401
CAS No:17360-11-1
Synonyms/Alias:17360-11-1;3,5-Dinitro-L-tyrosine;3,5-Dinitrotyrosine;(S)-2-Amino-3-(4-hydroxy-3,5-dinitrophenyl)propanoicacid;3,5-Dinitro-tyr-oh;CHEBI:28275;(2S)-2-amino-3-(4-hydroxy-3,5-dinitrophenyl)propanoicacid;Tyrosine,3,5-dinitro-;C03225;L-Tyrosine,3,5-dinitro-;AC1L98DC;SCHEMBL426451;CHEMBL2111693;CTK0H8249;SAZOSDSFLRXREA-YFKPBYRVSA-;MolPort-001-793-132;ANW-61119;H-Tyr(3,5-(NO2)2)-OH;ZINC12428290;AKOS015888308;AM83568;RTR-007691;VZ34913;3,5-Dinitro-4-hydroxy-L-phenylalanine;AJ-62261
3,5-Dinitro-L-tyrosine is a tyrosine-derived amino acid featuring two strongly electron-withdrawing nitro substituents on the aromatic ring, which makes it a useful structural and chemical handle for specialized peptide and protein chemistry. As an L-configured amino acid, it is commonly handled as a defined building block for incorporating a nitro-activated phenylalanine-like aromatic environment into peptide sequences, and it is also used as a reference material in analytical workflows where the dinitro-tyrosine motif is monitored. The nitro functionality enables distinct reactivity and mass/UV signatures that support downstream detection and characterization of nitro-substituted aromatic residues.
1. Nitro-Residue Peptide Building
3,5-Dinitro-L-tyrosine is used by peptide chemistry groups to prepare peptide segments and modified peptides that contain a dinitro-tyrosine aromatic residue for structure-property studies. Researchers commonly incorporate this residue into custom peptide synthesis to create defined aromatic electronic environments for studying how strongly electron-withdrawing substituents influence peptide conformation, intermolecular interactions, or chemical stability under assay conditions. Because the aromatic ring already bears the nitro pattern, it functions as a direct amino acid building block rather than requiring late-stage aromatic functionalization, which helps maintain sequence fidelity and simplify characterization of the final peptide.
2. Chemical Biology Labeling Standards
3,5-Dinitro-L-tyrosine is widely used as an analytical and method-development standard in chemical biology workflows that track nitro-substituted aromatic motifs in peptide or protein samples. Analytical chemists and proteomics method developers use it to calibrate identification and quantification of dinitro-tyrosine-containing species by LC-MS and related platforms, leveraging the characteristic mass shift and strong chromophore behavior associated with the dinitro aromatic ring. In practice, the defined L-amino acid identity supports reproducible reference preparation for monitoring derivatization efficiency, recovery, and signal consistency across batches of complex biological matrices.
3. Protein Modification Research
3,5-Dinitro-L-tyrosine supports protein engineering and protein modification studies where researchers need a defined nitro-activated tyrosine analog for mapping chemical reactivity or for validating analytical readouts. Protein chemists use it in model systems to generate peptide fragments or standards that reflect how dinitro-tyrosine-like aromatic environments behave during sample processing, digestion, and analytical measurement. This makes the reagent useful for method validation in workflows that assess aromatic residue modification patterns, differentiate closely related aromatic species, or benchmark chromatographic and mass spectrometric separation of nitro-substituted tyrosine analogs.
4. Pharmaceutical Intermediate Development
3,5-Dinitro-L-tyrosine is also used in industrial and medicinal chemistry development as a defined nitro-functionalized amino acid intermediate for downstream synthesis of specialty aromatic derivatives. Process and R&D chemists select this building block when a dinitro-phenyl motif is required as a protected/activated aromatic precursor in multistep routes, including the preparation of nitro-substituted aromatic intermediates used to access further functionalization patterns. Its fixed substitution pattern and L-amino acid identity make it a practical starting material for producing well-defined intermediates that can be characterized unambiguously before scale-up.
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